Ryan Kolofsky
SALES ENABLEMENT EXECUTIVE
About Me
I’m a passionate sales and revenue enablement leader dedicated to helping teams reach their full potential and drive revenue growth. With firsthand sales experience and a proven track record backed by multiple references, I know what it takes to succeed and deliver actual results. I’ve enhanced performance through strategic training, go-to-market plans, and operational improvements. At my core, I’m a people person who believes in building trust, listening closely, and nurturing talent. I bring positive, collaborative energy and am confident I’ll be an excellent fit for your culture. By blending sales methodologies with creative content and my expertise in revenue enablement, I drive lasting impact and measurable results.
Agile sales enablement executive driving performance
Master of the sales process, executive leadership, sales methodology, adult learning, and process improvement.
What I do
Sales
Elevate sales performance through strategic enablement, combining innovative content, agile methodologies, and targeted training to empower teams and achieve corporate growth objectives.
Team Development
Foster continuous learning, leadership development, and collaboration to drive team success. Empower individuals with tailored training programs that enhance skills and align with organizational goals.
Improve ramp-up time
Accelerate ramp-up time to first sale by 25-30% for Account Executives and Customer Success teams by developing tailored onboarding plans and effective training programs.
An accomplished ultra marathon runner
My Experience
2023-2024
HH2
Senior Director of Sales Training & Enablement
• Reduced ramp time by 30% by developing a comprehensive 3-week onboarding program for both AEs and BDRs.
• Increased sales performance by successfully launching the Highspot platform and completing two onboarding learning paths and certification programs.
• Improved consistency and efficiency by creating a step-by-step sales process
guide integrated with Highspot.
• Reduced Salesforce hygiene errors by 70% by designing a Process Library
featuring crucial Salesforce, Gong Engage, and ZoomInfo processes.
• Enhanced sales effectiveness by developing Sales Enablement Calendar, delivering bi-weekly training sessions tailored to the immediate needs of AEs and BDRs.
2022-2023
Kalderos
Senior Director of Sales Enablement
• Improved ramp time to first sale by 25% to 30% for Account Executives and
Customer Success teams by developing new onboarding plans.
• Standardized competency across teams by creating over 91 new training courses
and certification programs covering Buyer & User Persona, Competitive Intelligence,
Platform Demo, and more.
• Enhanced sales team focus by revamping pipeline review meetings through the
introduction of Gong Deal Dashboards.
• Implemented the Highspot platform to organize marketing content and make it readily available to the sales team.
• Implemented Highspot Sales Plays, increasing open rates of outreach by 9%
2021–2022
StructionSite
Director of Sales Enablement
• Addressed training needs across the organization by proactively working with
leaders at all levels and developing content that improved overall sales performance.
• Enhanced sales messaging by working closely with the Marketing department to
understand market trends and translate them into actionable insights for the sales
team.
• Implemented LevelJump Sales LMS and built out complete onboarding learning paths, resulting in decreasing AE ramp time by 30%
2020–2021
FairWarning/Imprivata
Director of Training & Enablement
• Improved competitive readiness by developing competitive messaging, battle
cards, and other materials to equip Sales and customer-facing teams for success in
competitive situations.
• Increased sales team alignment by educating Sales on processes, hand-offs, SLAs, commitments, and job expectations.
2019–2020
FairWarning/Imprivata
Sales Enablement Officer
• Aligned the sales team with corporate objectives by directing day-to-day
operations and onboarding of new sales development representatives.
• Improved individual and team performance by developing ongoing residual training programs.
2016–2018
MidAmerica Administrative and Retirement Solutions
Director – Learning & Development and Customer Service
• Improved workforce versatility by leading the implementation of an LMS and
developing a learning curriculum for cross-training and leadership development.
• Enhanced internal communication by creating the MARS Explore interactive
training tool, enabling front-line employees to create their own video training materials.
2015–2016
CSS Medical
Learning Development Manager
• Raised the company’s Net Promoter Score by 6% by developing customer
experience training and revitalizing the learning and development curriculum.
• Decreased product returns by 10% by innovating a process matrix and
implementing quality assurance and compliance training modules.
2014–2015
E-Telequote Insurance
Sales & Training Director
• Improved customer experience training, resulting in a 6% increase in the Net Promoter Score.
• Reduced product returns by 10% through innovative training modules focused on quality assurance and compliance.
2012–2014
Vology
Sales Training Manager
• Designed and executed comprehensive sales training programs that boosted team productivity and quota achievement.
• Implemented coaching techniques that improved individual sales rep performance and overall team outcomes.
2009–2012
Transact/TZ Insurance Solutions
Director of Training
• Led the development of training programs focused on improving sales processes and boosting overall team performance.
• Enhanced onboarding programs, resulting in faster ramp-up times for new hires and improved retention rates.
Education
Bachelor of Communications
University of South Florida
Associate of Arts Communications
St. Petersburg College
Certified DISC in the Workplace Facilitator
Awards
Outstanding Sales Support
Kalderos / 2022
MVP Award
FairWarning / 2021
MARS Employee of the Year
MidAmerica / 2017
Skills
Tools
LMS / Coaching & Analytics
CRM, CMS & Outreach
Collaboration & Content
Portfolio
